No matter how hard I wish for beach weather, the Boston forecast seems to be stuck in gloomy rain mode. As a result, I’ve been spending a lot of time daydreaming of a place where things aren’t so grey. I’m talking turquoise waters, white-sand beaches, palm trees…

I simply cannot get my mind off the Caribbean. So, in the name of daydreaming, I’ve crafted my own imaginary (for now) island itinerary where my days are filled with scouring local markets, dancing to reggae, cruising by sunset, and – of course – spending a hefty amount of time poolside. I’ve even gone ahead and planned my ever-so-stylish outfits, too. (Because you never know when someone might offer you a free flight.)